triphenyl(pyridin-2-yl)phosphonium trifluoromethanesulfonate | 116864-83-6

• 英文名称: triphenyl(pyridin-2-yl)phosphonium trifluoromethanesulfonate
• 英文别名: 2-pyridinyltriphenylphosphonium trifluoromethanesulfonate；Triphenyl(2-pyridyl)phosphonium-trifluormethansulfonat；triphenyl-2-pyridylphosphonium triflate；2-pyridyltriphenylphosphonium triflate
• CAS: 116864-83-6
• 化学式: CF₃O₃S*C₂₃H₁₉NP
• 分子量: 489.455
• InChiKey: YAZABLGBXCJTOS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  70.09
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  triphenyl(pyridin-2-yl)phosphonium trifluoromethanesulfonate 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  二阳离子cation盐：Mukaiyama-aldol反应的路易斯酸引发剂†

  摘要：

  两种策略用于制备离子型phospho阳离子。第一种方法是将1-氯环丙烯盐与膦反应，得到环丙烯取代的phospho盐10a-f [BF 4 ]。进行阴离子交换可得到相应的[B（C 6 F 5）4 ] -类似物10a-f [B（C 6 F 5）4 ]，后者在有机溶剂中的溶解度更高。此外，我们开发了包含2-，3-或4-甲基吡啶取代基11a–c [TfO]的二价phospho盐的合成方法，这些取代基也可以转化为它们的[B（C6 F 5） 4 ] -类似物11a–c [B（C 6 F 5）4 ]。最后，还制备了苯氧基取代的salt盐12 [B（C 6 F 5）4 ]。与它们的氟化类似物相比，所有盐在空气中均表现出显着的稳定性。通过理论计算评估了这些盐的路易斯酸度，最后证明它们在引发Mukaiyama-aldol反应方面是有效的。

  DOI：

  10.1039/c7dt03197a
• 作为产物：
  描述：

  2,4-Pyridindiylbis(triphenylphosphoniumtrifluormethansulfonat) 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以71%的产率得到triphenyl(pyridin-2-yl)phosphonium trifluoromethanesulfonate
  参考文献：
  名称：

  Anders, Ernst; Markus, Fritz, Chemische Berichte, 1989, vol. 122, p. 119 - 122

  摘要：

  DOI：

文献信息

• Synthesis of quaternary aryl phosphonium salts: photoredox-mediated phosphine arylation
  作者：A. F. Fearnley、J. An、M. Jackson、P. Lindovska、R. M. Denton

  DOI：10.1039/c6cc00556j

  日期：——

  We report a synthesis method for the construction of quaternary aryl phoshonium salts at ambient temperature.

  我们报告了一种在环境温度下构建季芳基磷鎓盐的合成方法。
• Preparation and Reaction of Quinolinyl (or Pyridinyl)phosphonium Salts with Base and Pivalaldehyde
  作者：Osamu Sugimoto、Minami Shimada、Akihiro Sato、Ken-ichi Tanji

  DOI：10.3987/com-11-12154

  日期：——

  alpha- and gamma-Heteroaryltriphenylphosphonium iodides were prepared by reaction of the corresponding heteroaryl iodides with triphenylphosphine. Reaction of beta-heteroaryl iodides with triphenylphosphine in the presence of a palladium catalyst gave beta-heteroaryltriphenylphosphonium iodides. Elimination of the heteroaryl group was achieved by treating the heteroaryltriphenylphosphonium iodides with a base. Further, the heteroaryl group was trapped with pivalaldehyde to introduce a pivaloyl substituent onto the heteroaromatic ring.
• Synthesis of Phosphonium Salts—Phosphine Structure and Inorganic Salts Effects
  作者：Mária Mečiarová、Štefan Toma、André Loupy、Branislav Horváth

  DOI：10.1080/10426500701545950

  日期：2007.12.24

  Solvent-free reactions of 2- and 3-halopyridines with PPh3, PBu3, and PCy3 were studied under conventional heating, as well as under microwave irradiation. No difference was observed in the reaction course between classical and microwave reactions. 2-Bromopyridine gave quantitative yields of 2-pyridyltriphenylphosphonium bromide within few minutes at 190 degrees C. Equimolar amounts of some inorganic salts (LiPF6, LiOTf, LiBr NaPF6, KPF6) were necessary for the reactions of the other 2-halopyridines. 3-Halopyridines did not react with PPh3 even in the presence of LiPF6. Their reactions with PCy3 in the presence of LiPF6 resulted in the quantitative formation of dicyclohexylphosphine oxide.